Table of Contents Author Guidelines Submit a Manuscript
Journal of Chemistry
Volume 2017, Article ID 6907421, 9 pages
https://doi.org/10.1155/2017/6907421
Research Article

Molecular Dynamics Study of the Factors Influencing the β-Cyclodextrin Inclusion Complex Formation of the Isomers of Linear Molecules

Departamento de Física, Universidad de La Laguna, La Laguna, 38206 Tenerife, Spain

Correspondence should be addressed to E. Alvira; se.llu@arivlam

Received 19 February 2017; Accepted 2 May 2017; Published 22 May 2017

Academic Editor: Jaime Villaverde

Copyright © 2017 E. Alvira. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. J. Szejtli and T. Osa, Comprehensive Supramolecular Chemistry, Pergamon/Elsevier, Oxford, United Kingdom, 1996.
  2. K. B. Lipkowitz, “Atomistic modeling of enantioselection in chromatography,” Journal of Chromatography A, vol. 906, no. 1-2, pp. 417–442, 2001. View at Publisher · View at Google Scholar · View at Scopus
  3. K. B. Lipkowitz, “Applications of computational chemistry to the study of cyclodextrins,” Chemical Reviews, vol. 98, no. 5, pp. 1829–1873, 1998. View at Publisher · View at Google Scholar · View at Scopus
  4. L. F. B. Malta, Y. Cordeiro, L. W. Tinoco, C. C. Campos, M. E. Medeiros, and O. A. C. Antunes, “Recognition mechanism of d- and l-tryptophan enantiomers using 2-hydroxypropyl-α- or β-cyclodextrins as chiral selectors,” Tetrahedron Asymmetry, vol. 19, no. 10, pp. 1182–1188, 2008. View at Publisher · View at Google Scholar · View at Scopus
  5. Y. Wang, T. S. Chung, H. Wang, and S. H. Goh, “Butanol isomer separation using polyamide-imide/CD mixed matrix membranes via pervaporation,” Chemical Engineering Science, vol. 64, no. 24, pp. 5198–5209, 2009. View at Publisher · View at Google Scholar · View at Scopus
  6. P. Brocos, N. Díaz-Vergara, X. Banquy, S. Pérez-Casas, M. Costas, and Á. Piñeiro, “Similarities and differences between cyclodextrin-sodium dodecyl sulfate host-guest complexes of different stoichiometries: molecular dynamics simulations at several temperatures,” Journal of Physical Chemistry B, vol. 114, no. 39, pp. 12455–12467, 2010. View at Publisher · View at Google Scholar · View at Scopus
  7. G. González-Gaitano, P. R. Sainz-Rozas, J. R. Isasi, A. Guerrero-Martínez, and G. Tardajos, “Site-specific interaction between 2-dibenzofuran carboxylate and β- And γ-cyclodextrins determined by intermolecular NOE and molecular modeling,” Journal of Physical Chemistry B, vol. 108, no. 37, pp. 14154–14162, 2004. View at Publisher · View at Google Scholar · View at Scopus
  8. L. Seridi and A. Boufelfel, “Simulations of docking C60 in β-Cyclodextrin,” Journal of Molecular Liquids, vol. 162, no. 2, pp. 69–77, 2011. View at Publisher · View at Google Scholar · View at Scopus
  9. A. A. Elbashir and F. O. Suliman, “Computational modeling of capillary electrophoretic behavior of primary amines using dual system of 18-crown-6 and β-cyclodextrin,” Journal of Chromatography A, vol. 1218, no. 31, pp. 5344–5351, 2011. View at Publisher · View at Google Scholar · View at Scopus
  10. Y. Luo, B. Egwolf, D. E. Walters, and B. Roux, “Ion selectivity of α-hemolysin with a β-cyclodextrin adapter. I. single ion potential of mean force and diffusion coefficient,” Journal of Physical Chemistry B, vol. 114, no. 2, pp. 952–958, 2010. View at Publisher · View at Google Scholar · View at Scopus
  11. T. Wang, C. Chipot, X. Shao, and W. Cai, “Structural characterization of micelles formed of cholesteryl- functionalized cyclodextrins,” Langmuir, vol. 27, no. 1, pp. 91–97, 2011. View at Publisher · View at Google Scholar · View at Scopus
  12. P. Cairo, F. Ortuso, S. Alcaro, E. Fontananova, E. Tocci, and E. Drioli, “β-cyclodextrin interactions with three drugs used in inflammatory pathologies: an experimental and theoretical study,” Chemical Physics Letters, vol. 454, no. 4-6, pp. 374–381, 2008. View at Publisher · View at Google Scholar · View at Scopus
  13. E. Alvira, “Molecular modelling study of β-cyclodextrin inclusion complexes,” Chemical Physics Letters, vol. 271, pp. 178–184, 1997. View at Publisher · View at Google Scholar · View at Scopus
  14. E. Alvira, “Capacity of small molecules to form β-cyclodextrin inclusion complexes,” Supramolecular Chemistry, vol. 22, no. 3, pp. 156–162, 2010. View at Publisher · View at Google Scholar · View at Scopus
  15. E. Alvira, “A continuum model for van der waals interaction between β-cyclodextrin and linear molecules: part 1,” Chemical Physics Letters, vol. 439, pp. 252–257, 2007. View at Publisher · View at Google Scholar · View at Scopus
  16. E. Alvira, “Mobility of linear molecules inside and around β-cyclodextrin,” Molecular Physics, vol. 107, no. 16, pp. 1697–1704, 2009. View at Publisher · View at Google Scholar · View at Scopus
  17. E. Alvira, “A continuum model for van der waals interaction between β-cyclodextrin and linear molecules: part 2,” Chemical Physics Letters, vol. 439, pp. 258–263, 2007. View at Publisher · View at Google Scholar · View at Scopus
  18. E. Alvira, “Simulation of the physisorption of linear molecules in β-cyclodextrin,” Journal of Inclusion Phenomena and Macrocyclic Chemistry, vol. 57, no. 1-4, pp. 619–623, 2007. View at Publisher · View at Google Scholar · View at Scopus
  19. E. Alvira, “Stereochemical features of the physisorption of linear molecules in β-cyclodextrin,” Supramolecular Chemistry, vol. 23, no. 7, pp. 550–557, 2011. View at Publisher · View at Google Scholar · View at Scopus
  20. K. B. Lipkowitz, G. Pearl, B. Coner, and M. A. Peterson, “Explanation of where and how enantioselective binding takes place on permethylated β-cyclodextrin, a chiral stationary phase used in gas chromatography,” Journal of the American Chemical Society, vol. 119, no. 3, pp. 600–610, 1997. View at Publisher · View at Google Scholar · View at Scopus
  21. K. B. Lipkowitz, R. Coner, and M. A. Peterson, “Locating regions of maximum chiral discrimination: a computational study of enantioselection on a popular chiral stationary phase used in chromatography,” Journal of the American Chemical Society, vol. 119, no. 46, pp. 11269–11276, 1997. View at Publisher · View at Google Scholar · View at Scopus
  22. J. Israelachvili, Intermolecular and Surfaces Forces, Academic Press, San Diego, CA, USA, 1995.
  23. A. J. Stone, The Theory of Intermolecular Forces, Oxford University Press, New York, NY, USA, 1996.
  24. L. W. Bruch, M. W. Cole, and E. Zaremba, Physical Adsorption: Forces and Phenomena, Clarendon Press, Oxford, United Kingdom, 1997.
  25. D. Frenkel and B. Smit, Understanding Molecular Simulation, Academic Press, San Diego, CA, USA, 2002.
  26. D. C. Rapaport, The Art of Molecular Dynamics Simulation, Cambridge University Press, Cambridge, United Kingdom, 1995.
  27. M. P. Allen and D. J. Tildesley, Journal of Solution Chemistry, Clarendon Press, Oxford, United Kingdom, 1987.
  28. E. Alvira, “Theoretical study of the separation of valine enantiomers by β-cyclodextrin with different solvents: a molecular mechanics and dynamics simulation,” Tetrahedron Asymmetry, vol. 26, no. 15-16, Article ID 59328, pp. 853–860, 2015. View at Publisher · View at Google Scholar · View at Scopus
  29. D. Brown and J. H. R. Clarke, “A comparison of constant energy, constant temperature and constant pressure ensembles in molecular dynamics simulations of atomic liquids,” Molecular Physics, vol. 51, no. 5, pp. 1243–1252, 1984. View at Publisher · View at Google Scholar · View at Scopus
  30. D. Fincham, N. Quirke, and D. J. Tildesley, “Computer simulation of molecular liquid mixtures. I. A diatomic Lennard-Jones model mixture for CO2/C2H6,” Journal of Chemical Physics, vol. 84, pp. 4535–4541, 1986. View at Publisher · View at Google Scholar
  31. S. Nishikawa, K. Yamaguchi, and T. Fukahori, “Ultrasonic relaxation due to complexation reaction between β-cyclodextrin and alkylammonium ions,” Journal of Physical Chemistry A, vol. 107, no. 33, pp. 6415–6418, 2003. View at Publisher · View at Google Scholar · View at Scopus
  32. K. Yamaguchi, T. Fukahori, and S. Nishikawa, “Dynamic Interaction between Alkylammonium Ions and β-cyclodextrin by means of ultrasonic Relaxation,” Journal of Physical Chemistry A, vol. 109, no. 1, pp. 40–43, 2005. View at Publisher · View at Google Scholar · View at Scopus
  33. C. B'Hymer, “Evaluation and validation of an HPLC procedure for the determination of the positional isomeric impurity in 2-[4-(1-hydroxy-4-[4-(hydroxydiphenylmethyl)-1- piperidinyl]-butyl)-phenyl]-2-methylpropionic acid,” Journal of Analytical Chemistry, vol. 63, no. 4, pp. 376–380, 2008. View at Publisher · View at Google Scholar · View at Scopus
  34. N. K. Sangwan and H.-J. Schneider, “The kinetic effects of water and of cyclodextrins on Diels-Alder reactions. Host-guest chemistry. Part 18,” Journal of the Chemical Society, Perkin Transactions 2, no. 9, pp. 1223–1227, 1989. View at Google Scholar · View at Scopus